Structure

Physi-Chem Properties

Molecular Weight:  240.08
Volume:  250.242
LogP:  3.561
LogD:  2.615
LogS:  -3.769
# Rotatable Bonds:  0
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.653
Synthetic Accessibility Score:  3.426
Fsp3:  0.133
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.936
MDCK Permeability:  6.687766926916083e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.017
20% Bioavailability (F20%):  0.043
30% Bioavailability (F30%):  0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.04
Plasma Protein Binding (PPB):  91.21309661865234%
Volume Distribution (VD):  0.751
Pgp-substrate:  6.197897911071777%

ADMET: Metabolism

CYP1A2-inhibitor:  0.98
CYP1A2-substrate:  0.815
CYP2C19-inhibitor:  0.47
CYP2C19-substrate:  0.137
CYP2C9-inhibitor:  0.58
CYP2C9-substrate:  0.688
CYP2D6-inhibitor:  0.66
CYP2D6-substrate:  0.392
CYP3A4-inhibitor:  0.172
CYP3A4-substrate:  0.118

ADMET: Excretion

Clearance (CL):  2.444
Half-life (T1/2):  0.469

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.334
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.56
Rat Oral Acute Toxicity:  0.975
Maximum Recommended Daily Dose:  0.768
Skin Sensitization:  0.779
Carcinogencity:  0.919
Eye Corrosion:  0.065
Eye Irritation:  0.809
Respiratory Toxicity:  0.902

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC13784

Natural Product ID:  NPC13784
Common Name*:   Mansonone F
IUPAC Name:   n.a.
Synonyms:   Mansonone F
Standard InCHIKey:  WSRLWSPFIOAYST-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H12O3/c1-7-4-5-10-8(2)6-18-15-9(3)13(16)14(17)11(7)12(10)15/h4-6H,1-3H3
SMILES:  Cc1ccc2C(=COC3=C(C)C(=O)C(=O)c1c23)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL197655
PubChem CID:   94304
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0000153] Naphthoquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO6427 Wardomyces anomalus Species Microascaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/np020518b]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota root bark Kuantaochi, Nantou Hsien, Taiwan n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota stem bark;fruit n.a. n.a. PMID[10924160]
NPO6427 Wardomyces anomalus Species Microascaceae Eukaryota n.a. n.a. n.a. PMID[12762814]
NPO19460 Karenia brevis Species Kareniaceae Eukaryota n.a. n.a. n.a. PMID[15679307]
NPO3895 Gynerium sagittatum Species Poaceae Eukaryota n.a. n.a. n.a. PMID[17442349]
NPO5167 Peripentadenia mearsii Species Elaeocarpaceae Eukaryota n.a. Australian rainforest n.a. PMID[18039010]
NPO19367 Thespesia populnea Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[18553924]
NPO19460 Karenia brevis Species Kareniaceae Eukaryota n.a. n.a. n.a. PMID[20218657]
NPO7073 Prorocentrum maculosum Species Prorocentraceae Eukaryota n.a. n.a. n.a. PMID[8946740]
NPO10455 Vaccinium uliginosum Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19367 Thespesia populnea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10455 Vaccinium uliginosum Species Ericaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO960 Phlomis aurea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19367 Thespesia populnea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25170 Dictyota coriacea Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7535 Mansonia altissima Species Culicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11354 Streptomyces galbus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9794 Dysoxylum fraseranum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6878 Vesperus xatarti Species Cerambycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6427 Wardomyces anomalus Species Microascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2181 Erodium chium Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11510 Astragalus flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24924 Saara hardwickii Species Agamidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5758 Licania crassifolia Species Chrysobalanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12123 Geodia gigas Species Geodiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7073 Prorocentrum maculosum Species Prorocentraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3895 Gynerium sagittatum Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10273 Dictyota flabellata Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19367 Thespesia populnea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8699 Azanza garckeana Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5167 Peripentadenia mearsii Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4348 Watasenia scintillans Species Enoploteuthidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10455 Vaccinium uliginosum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO329 Arum cucullatum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9565 Linum maritimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO960 Phlomis aurea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17202 Lasallia asiae-orientalis Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1732 Ligularia franchetiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3546 Shorea balangeran Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4060 Carduus assoi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25866 Kaunia lasiophthalma Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8878 Polygala arenaria Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4583 Agathosma gnidioides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2124 Bulgaria inquinans Species Bulgariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13058 Psychotria brachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2066 Streptomyces ipomoeae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11158 Diplopterygium rufopilosum Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6423 Vitex cauliflora Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19460 Karenia brevis Species Kareniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25170 Dictyota coriacea Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 1782.38 nM PMID[505659]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 3706.81 nM PMID[505659]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 2837.92 nM PMID[505659]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 8298.51 nM PMID[505659]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 14655.48 nM PMID[505659]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 15631.48 nM PMID[505659]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 2098.94 nM PMID[505659]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 6208.69 nM PMID[505659]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 3213.66 nM PMID[505659]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 1686.55 nM PMID[505659]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 859.01 nM PMID[505659]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 3664.38 nM PMID[505659]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 20090.93 nM PMID[505659]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 349.14 nM PMID[505659]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 4518.56 nM PMID[505659]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 2564.48 nM PMID[505659]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 2098.94 nM PMID[505659]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 4375.22 nM PMID[505659]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 2703.96 nM PMID[505659]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 18238.96 nM PMID[505659]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 4073.8 nM PMID[505659]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 3451.44 nM PMID[505659]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 3280.95 nM PMID[505659]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 42072.66 nM PMID[505659]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 2612.16 nM PMID[505659]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 3926.45 nM PMID[505659]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 2172.7 nM PMID[505659]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 2864.18 nM PMID[505659]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 1419.06 nM PMID[505659]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 2648.5 nM PMID[505659]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2773.32 nM PMID[505659]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 14223.29 nM PMID[505659]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 3655.95 nM PMID[505659]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 5559.04 nM PMID[505659]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 2924.15 nM PMID[505659]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 9057.33 nM PMID[505659]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 6266.14 nM PMID[505659]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 2426.61 nM PMID[505659]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 2606.15 nM PMID[505659]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 4436.09 nM PMID[505659]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 2691.53 nM PMID[505659]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 6918.31 nM PMID[505659]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 2494.59 nM PMID[505659]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 8241.38 nM PMID[505659]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 15848.93 nM PMID[505659]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 3235.94 nM PMID[505659]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 2182.73 nM PMID[505659]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 20323.57 nM PMID[505659]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1901.08 nM PMID[505659]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 3741.11 nM PMID[505659]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 5482.77 nM PMID[505659]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 17741.89 nM PMID[505659]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 7227.7 nM PMID[505659]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 4102.04 nM PMID[505659]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 2978.52 nM PMID[505659]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 14421.15 nM PMID[505659]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 3147.75 nM PMID[505659]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 14157.94 nM PMID[505659]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 2552.7 nM PMID[505659]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 7177.94 nM PMID[505659]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC50 = 2.0 ug.mL-1 PMID[505656]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC90 = 4.0 ug.mL-1 PMID[505656]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 2.0 ug.mL-1 PMID[505656]
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 4.0 ug.mL-1 PMID[505656]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 1.0 ug.mL-1 PMID[505656]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 4.0 ug.mL-1 PMID[505656]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 0.5 ug.mL-1 PMID[505656]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC = 8.0 ug.mL-1 PMID[505656]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 8.0 ug.mL-1 PMID[505656]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 1.0 ug.mL-1 PMID[505656]
NPT35 Others n.a. Activity = 14.0 microM/min PMID[505657]
NPT35 Others n.a. Activity = 58.0 microM/min PMID[505657]
NPT1266 Organism Leptomonas seymouri Leptomonas seymouri IC50 = 100.0 nM PMID[505657]
NPT1267 Organism Crithidia fasciculata Crithidia fasciculata IC50 = 300.0 nM PMID[505657]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 15530.0 nM PMID[505658]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 27340.0 nM PMID[505658]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC13784 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9811 High Similarity NPC228936
0.9537 High Similarity NPC135730
0.9352 High Similarity NPC196075
0.9167 High Similarity NPC212415
0.9115 High Similarity NPC289432
0.9115 High Similarity NPC988
0.9035 High Similarity NPC144547
0.9 High Similarity NPC477411
0.8947 High Similarity NPC238861
0.8947 High Similarity NPC77000
0.8839 High Similarity NPC226093
0.875 High Similarity NPC474095
0.8727 High Similarity NPC210089
0.8644 High Similarity NPC51079
0.8621 High Similarity NPC232958
0.8559 High Similarity NPC291799
0.8455 Intermediate Similarity NPC470391
0.844 Intermediate Similarity NPC209632
0.8426 Intermediate Similarity NPC60679
0.8421 Intermediate Similarity NPC470764
0.8421 Intermediate Similarity NPC474408
0.8393 Intermediate Similarity NPC137315
0.8393 Intermediate Similarity NPC474157
0.8349 Intermediate Similarity NPC114594
0.8319 Intermediate Similarity NPC79496
0.8246 Intermediate Similarity NPC272524
0.823 Intermediate Similarity NPC474057
0.823 Intermediate Similarity NPC167504
0.8214 Intermediate Similarity NPC99846
0.8214 Intermediate Similarity NPC83628
0.8214 Intermediate Similarity NPC265407
0.8214 Intermediate Similarity NPC269023
0.8214 Intermediate Similarity NPC192577
0.8198 Intermediate Similarity NPC30594
0.8198 Intermediate Similarity NPC37622
0.8174 Intermediate Similarity NPC326664
0.8174 Intermediate Similarity NPC308744
0.8174 Intermediate Similarity NPC196673
0.8142 Intermediate Similarity NPC273837
0.8125 Intermediate Similarity NPC203732
0.8115 Intermediate Similarity NPC295664
0.8108 Intermediate Similarity NPC172483
0.8103 Intermediate Similarity NPC474685
0.8103 Intermediate Similarity NPC210092
0.8073 Intermediate Similarity NPC112552
0.8065 Intermediate Similarity NPC428300
0.8036 Intermediate Similarity NPC119271
0.8018 Intermediate Similarity NPC31786
0.8017 Intermediate Similarity NPC241851
0.8017 Intermediate Similarity NPC67377
0.7984 Intermediate Similarity NPC177925
0.7969 Intermediate Similarity NPC310662
0.7969 Intermediate Similarity NPC59459
0.7965 Intermediate Similarity NPC56493
0.7949 Intermediate Similarity NPC306740
0.7944 Intermediate Similarity NPC5472
0.7937 Intermediate Similarity NPC57552
0.7934 Intermediate Similarity NPC472981
0.7928 Intermediate Similarity NPC274443
0.7928 Intermediate Similarity NPC89886
0.7917 Intermediate Similarity NPC204784
0.7909 Intermediate Similarity NPC70624
0.7899 Intermediate Similarity NPC228318
0.7895 Intermediate Similarity NPC17417
0.7895 Intermediate Similarity NPC10251
0.7891 Intermediate Similarity NPC183103
0.7886 Intermediate Similarity NPC228739
0.7886 Intermediate Similarity NPC182646
0.7881 Intermediate Similarity NPC149691
0.7881 Intermediate Similarity NPC471616
0.7863 Intermediate Similarity NPC307651
0.7845 Intermediate Similarity NPC270699
0.7845 Intermediate Similarity NPC82899
0.784 Intermediate Similarity NPC474737
0.7838 Intermediate Similarity NPC222390
0.7838 Intermediate Similarity NPC188895
0.7838 Intermediate Similarity NPC244427
0.7833 Intermediate Similarity NPC318173
0.7826 Intermediate Similarity NPC251854
0.7826 Intermediate Similarity NPC174099
0.7826 Intermediate Similarity NPC93084
0.7826 Intermediate Similarity NPC196246
0.7826 Intermediate Similarity NPC214067
0.7818 Intermediate Similarity NPC203925
0.7815 Intermediate Similarity NPC190298
0.7812 Intermediate Similarity NPC279596
0.7812 Intermediate Similarity NPC239134
0.7805 Intermediate Similarity NPC65627
0.7805 Intermediate Similarity NPC223351
0.7798 Intermediate Similarity NPC249912
0.7798 Intermediate Similarity NPC92754
0.7798 Intermediate Similarity NPC276775
0.7778 Intermediate Similarity NPC128368
0.7778 Intermediate Similarity NPC130398
0.7768 Intermediate Similarity NPC474365
0.7768 Intermediate Similarity NPC301943
0.776 Intermediate Similarity NPC236405
0.7759 Intermediate Similarity NPC1082
0.7759 Intermediate Similarity NPC243355
0.7759 Intermediate Similarity NPC305912
0.7759 Intermediate Similarity NPC260818
0.775 Intermediate Similarity NPC323440
0.775 Intermediate Similarity NPC80605
0.775 Intermediate Similarity NPC222968
0.7748 Intermediate Similarity NPC42211
0.7739 Intermediate Similarity NPC85493
0.7736 Intermediate Similarity NPC173413
0.7727 Intermediate Similarity NPC225060
0.7727 Intermediate Similarity NPC78701
0.7727 Intermediate Similarity NPC35448
0.771 Intermediate Similarity NPC217914
0.771 Intermediate Similarity NPC309056
0.7705 Intermediate Similarity NPC476225
0.7698 Intermediate Similarity NPC51292
0.7692 Intermediate Similarity NPC470406
0.7692 Intermediate Similarity NPC321852
0.7692 Intermediate Similarity NPC292834
0.7692 Intermediate Similarity NPC23332
0.7679 Intermediate Similarity NPC45613
0.7674 Intermediate Similarity NPC164295
0.7674 Intermediate Similarity NPC477412
0.7667 Intermediate Similarity NPC158157
0.7664 Intermediate Similarity NPC133461
0.7658 Intermediate Similarity NPC146351
0.7658 Intermediate Similarity NPC118343
0.7656 Intermediate Similarity NPC471832
0.7652 Intermediate Similarity NPC211439
0.7647 Intermediate Similarity NPC221275
0.7638 Intermediate Similarity NPC51448
0.7638 Intermediate Similarity NPC115797
0.7638 Intermediate Similarity NPC45537
0.7634 Intermediate Similarity NPC212207
0.7634 Intermediate Similarity NPC1249
0.7632 Intermediate Similarity NPC134120
0.7627 Intermediate Similarity NPC143768
0.7627 Intermediate Similarity NPC161611
0.7623 Intermediate Similarity NPC201284
0.7615 Intermediate Similarity NPC260233
0.7615 Intermediate Similarity NPC477407
0.7615 Intermediate Similarity NPC477406
0.7612 Intermediate Similarity NPC470407
0.7611 Intermediate Similarity NPC247976
0.7607 Intermediate Similarity NPC265513
0.7607 Intermediate Similarity NPC183648
0.7603 Intermediate Similarity NPC469954
0.7603 Intermediate Similarity NPC45794
0.76 Intermediate Similarity NPC328107
0.76 Intermediate Similarity NPC318067
0.76 Intermediate Similarity NPC85511
0.7597 Intermediate Similarity NPC27659
0.7594 Intermediate Similarity NPC186647
0.7594 Intermediate Similarity NPC301341
0.7594 Intermediate Similarity NPC284184
0.7593 Intermediate Similarity NPC153885
0.7593 Intermediate Similarity NPC155232
0.7586 Intermediate Similarity NPC474364
0.7586 Intermediate Similarity NPC318327
0.7586 Intermediate Similarity NPC469636
0.7583 Intermediate Similarity NPC100353
0.7576 Intermediate Similarity NPC22644
0.7565 Intermediate Similarity NPC185763
0.7565 Intermediate Similarity NPC83409
0.7563 Intermediate Similarity NPC279916
0.7563 Intermediate Similarity NPC153053
0.7561 Intermediate Similarity NPC105709
0.7559 Intermediate Similarity NPC474264
0.7557 Intermediate Similarity NPC263817
0.7547 Intermediate Similarity NPC157778
0.7542 Intermediate Similarity NPC280789
0.7542 Intermediate Similarity NPC186128
0.7542 Intermediate Similarity NPC66208
0.7542 Intermediate Similarity NPC471188
0.7541 Intermediate Similarity NPC171023
0.754 Intermediate Similarity NPC75432
0.7538 Intermediate Similarity NPC205360
0.7524 Intermediate Similarity NPC307
0.7524 Intermediate Similarity NPC160339
0.7523 Intermediate Similarity NPC289883
0.7523 Intermediate Similarity NPC238219
0.7522 Intermediate Similarity NPC25458
0.752 Intermediate Similarity NPC217756
0.752 Intermediate Similarity NPC307174
0.7519 Intermediate Similarity NPC82712
0.7519 Intermediate Similarity NPC471670
0.7519 Intermediate Similarity NPC232996
0.7518 Intermediate Similarity NPC117674
0.75 Intermediate Similarity NPC476357
0.75 Intermediate Similarity NPC186933
0.75 Intermediate Similarity NPC23894
0.75 Intermediate Similarity NPC50872
0.75 Intermediate Similarity NPC274876
0.75 Intermediate Similarity NPC274839
0.75 Intermediate Similarity NPC112903
0.75 Intermediate Similarity NPC470007
0.75 Intermediate Similarity NPC325497
0.75 Intermediate Similarity NPC93181
0.75 Intermediate Similarity NPC476042
0.7481 Intermediate Similarity NPC476644
0.748 Intermediate Similarity NPC476599
0.7479 Intermediate Similarity NPC474176

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC13784 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9167 High Similarity NPD1609 Clinical (unspecified phase)
0.8947 High Similarity NPD3412 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.8018 Intermediate Similarity NPD164 Approved
0.7895 Intermediate Similarity NPD2182 Approved
0.7661 Intermediate Similarity NPD3972 Approved
0.7658 Intermediate Similarity NPD1238 Approved
0.7623 Intermediate Similarity NPD1651 Approved
0.7563 Intermediate Similarity NPD1241 Discontinued
0.7519 Intermediate Similarity NPD7008 Discontinued
0.7519 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5951 Approved
0.7477 Intermediate Similarity NPD3495 Discontinued
0.7458 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD650 Approved
0.744 Intermediate Similarity NPD1281 Approved
0.7402 Intermediate Similarity NPD1876 Approved
0.7391 Intermediate Similarity NPD1237 Approved
0.736 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD7609 Phase 3
0.7302 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD2346 Discontinued
0.7273 Intermediate Similarity NPD7631 Approved
0.7266 Intermediate Similarity NPD1283 Approved
0.7244 Intermediate Similarity NPD4878 Approved
0.7241 Intermediate Similarity NPD5909 Discontinued
0.7213 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD6287 Discontinued
0.7155 Intermediate Similarity NPD1929 Approved
0.7155 Intermediate Similarity NPD1930 Approved
0.7155 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD2798 Approved
0.7083 Intermediate Similarity NPD2067 Discontinued
0.708 Intermediate Similarity NPD1989 Approved
0.7068 Intermediate Similarity NPD2313 Discontinued
0.7063 Intermediate Similarity NPD5691 Approved
0.7054 Intermediate Similarity NPD1202 Approved
0.7043 Intermediate Similarity NPD2066 Phase 3
0.7037 Intermediate Similarity NPD9257 Approved
0.7037 Intermediate Similarity NPD9259 Approved
0.7031 Intermediate Similarity NPD1201 Approved
0.7029 Intermediate Similarity NPD1471 Phase 3
0.7016 Intermediate Similarity NPD3317 Approved
0.7015 Intermediate Similarity NPD7713 Phase 3
0.7 Intermediate Similarity NPD7003 Approved
0.6984 Remote Similarity NPD9545 Approved
0.6972 Remote Similarity NPD1087 Approved
0.6963 Remote Similarity NPD2979 Phase 3
0.696 Remote Similarity NPD405 Clinical (unspecified phase)
0.6947 Remote Similarity NPD3267 Approved
0.6947 Remote Similarity NPD1470 Approved
0.6947 Remote Similarity NPD3266 Approved
0.6923 Remote Similarity NPD1932 Approved
0.6906 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6899 Remote Similarity NPD518 Clinical (unspecified phase)
0.6884 Remote Similarity NPD3748 Approved
0.6875 Remote Similarity NPD4626 Approved
0.6861 Remote Similarity NPD1607 Approved
0.6849 Remote Similarity NPD3226 Approved
0.6842 Remote Similarity NPD1693 Approved
0.6842 Remote Similarity NPD688 Clinical (unspecified phase)
0.6838 Remote Similarity NPD4307 Phase 2
0.6835 Remote Similarity NPD2796 Approved
0.6825 Remote Similarity NPD9493 Approved
0.6822 Remote Similarity NPD4879 Approved
0.6818 Remote Similarity NPD1282 Approved
0.6815 Remote Similarity NPD3764 Approved
0.6809 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6797 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6786 Remote Similarity NPD1089 Approved
0.6786 Remote Similarity NPD1090 Approved
0.6786 Remote Similarity NPD1086 Approved
0.6786 Remote Similarity NPD9258 Approved
0.6786 Remote Similarity NPD9256 Approved
0.6783 Remote Similarity NPD7236 Approved
0.6774 Remote Similarity NPD7094 Approved
0.6774 Remote Similarity NPD6858 Approved
0.6767 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6763 Remote Similarity NPD2799 Discontinued
0.6763 Remote Similarity NPD1510 Phase 2
0.6763 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6754 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6754 Remote Similarity NPD1563 Approved
0.6744 Remote Similarity NPD2932 Approved
0.6744 Remote Similarity NPD17 Approved
0.6741 Remote Similarity NPD6039 Approved
0.6735 Remote Similarity NPD7458 Discontinued
0.6729 Remote Similarity NPD942 Approved
0.6726 Remote Similarity NPD1239 Approved
0.6721 Remote Similarity NPD2329 Discontinued
0.672 Remote Similarity NPD6010 Discontinued
0.6715 Remote Similarity NPD3142 Approved
0.6715 Remote Similarity NPD3140 Approved
0.6715 Remote Similarity NPD1240 Approved
0.6714 Remote Similarity NPD2438 Suspended
0.6714 Remote Similarity NPD2531 Phase 2
0.6713 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6696 Remote Similarity NPD800 Approved
0.6692 Remote Similarity NPD2797 Approved
0.6691 Remote Similarity NPD3268 Approved
0.6667 Remote Similarity NPD3025 Approved
0.6667 Remote Similarity NPD6832 Phase 2
0.6667 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1508 Approved
0.6667 Remote Similarity NPD3024 Approved
0.6667 Remote Similarity NPD9495 Approved
0.6667 Remote Similarity NPD182 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7239 Suspended
0.6667 Remote Similarity NPD1088 Approved
0.6644 Remote Similarity NPD6273 Approved
0.6643 Remote Similarity NPD3750 Approved
0.6643 Remote Similarity NPD4308 Phase 3
0.6643 Remote Similarity NPD4628 Phase 3
0.6642 Remote Similarity NPD8032 Phase 2
0.6622 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6622 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6615 Remote Similarity NPD3019 Approved
0.6614 Remote Similarity NPD4198 Discontinued
0.6593 Remote Similarity NPD9494 Approved
0.6591 Remote Similarity NPD1608 Approved
0.6589 Remote Similarity NPD7009 Phase 2
0.6583 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6581 Remote Similarity NPD1564 Approved
0.6581 Remote Similarity NPD1565 Approved
0.6581 Remote Similarity NPD1566 Phase 3
0.6575 Remote Similarity NPD2532 Approved
0.6575 Remote Similarity NPD2534 Approved
0.6575 Remote Similarity NPD2533 Approved
0.6575 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6565 Remote Similarity NPD3023 Approved
0.6565 Remote Similarity NPD3026 Approved
0.6556 Remote Similarity NPD7819 Suspended
0.6552 Remote Similarity NPD9260 Approved
0.6549 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6549 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6549 Remote Similarity NPD2344 Approved
0.6542 Remote Similarity NPD9490 Approved
0.6541 Remote Similarity NPD5157 Phase 1
0.6541 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6541 Remote Similarity NPD5159 Phase 2
0.6535 Remote Similarity NPD2629 Approved
0.6529 Remote Similarity NPD3046 Approved
0.6529 Remote Similarity NPD3047 Approved
0.6529 Remote Similarity NPD3048 Approved
0.6519 Remote Similarity NPD2788 Approved
0.6519 Remote Similarity NPD1019 Discontinued
0.6519 Remote Similarity NPD6085 Phase 2
0.6519 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6515 Remote Similarity NPD1611 Approved
0.6513 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6512 Remote Similarity NPD7610 Discontinued
0.6503 Remote Similarity NPD970 Clinical (unspecified phase)
0.6503 Remote Similarity NPD1549 Phase 2
0.65 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6496 Remote Similarity NPD1843 Approved
0.6493 Remote Similarity NPD2199 Approved
0.6493 Remote Similarity NPD2198 Approved
0.6493 Remote Similarity NPD5667 Approved
0.6491 Remote Similarity NPD3673 Approved
0.6491 Remote Similarity NPD3672 Approved
0.6489 Remote Similarity NPD5126 Approved
0.6489 Remote Similarity NPD5125 Phase 3
0.6486 Remote Similarity NPD920 Approved
0.6481 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6479 Remote Similarity NPD4476 Approved
0.6479 Remote Similarity NPD2935 Discontinued
0.6479 Remote Similarity NPD4477 Approved
0.6475 Remote Similarity NPD3373 Approved
0.6466 Remote Similarity NPD6637 Approved
0.6466 Remote Similarity NPD9717 Approved
0.6463 Remote Similarity NPD642 Clinical (unspecified phase)
0.6463 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6462 Remote Similarity NPD1894 Discontinued
0.6458 Remote Similarity NPD1243 Approved
0.6455 Remote Similarity NPD9491 Approved
0.6446 Remote Similarity NPD9261 Approved
0.6438 Remote Similarity NPD643 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4622 Approved
0.6429 Remote Similarity NPD4618 Approved
0.6424 Remote Similarity NPD5889 Approved
0.6424 Remote Similarity NPD5890 Approved
0.6423 Remote Similarity NPD3134 Approved
0.6423 Remote Similarity NPD7055 Discontinued
0.6414 Remote Similarity NPD8166 Discontinued
0.6414 Remote Similarity NPD1878 Clinical (unspecified phase)
0.64 Remote Similarity NPD1317 Discontinued
0.6397 Remote Similarity NPD4980 Approved
0.6395 Remote Similarity NPD3950 Discontinued
0.6377 Remote Similarity NPD6966 Discovery
0.6371 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6371 Remote Similarity NPD1358 Approved
0.637 Remote Similarity NPD2309 Approved
0.637 Remote Similarity NPD3887 Approved
0.6369 Remote Similarity NPD6232 Discontinued
0.6364 Remote Similarity NPD5408 Approved
0.6364 Remote Similarity NPD5406 Approved
0.6364 Remote Similarity NPD1778 Approved
0.6364 Remote Similarity NPD5404 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data